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alpha-Bromo-o-fluorotoluene → Ethyl 1-benzyl-4-(2-fluorobenzyl)piperidine-4-carboxylate

HRID 270042
Notes
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Reaction equation

HRID 270042 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32]Br>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:32][C:31]2[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=2[F:29])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 67968alpha-Bromo-o-fluorotolueneHCID 90423Ethyl 1-benzylpiperidine-4-carboxylateHCID 2733832Lithium hexamethyldisilazane

Product 1

HCID 59833634Ethyl 1-benzyl-4-(2-fluorobenzyl)piperidine-4-carboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Ethyl 1-benzylpiperidine-4-carboxylate (2.47 g, 10 mmol) was dissolved in tetrahydrofuran (20 mL) and cooled to −78° C. Lithium bis(trimethylsilyl)amide (11 mL, 1.0 M in tetrahydrofuran) was added slowly, and stirred for 30 minutes. 2-fluoro-benzylbromide (1.34 mL, 11 mmol) in 5 mL tetrahydrofuran was added slowly. The resulting solution was allowed to reach room temperature and stirred over night. The reaction was quenched with ammonium chloride (aq, sat) and partitioned between water and ethyl acetate. The organic layer was washed with brine and dried over magnesium sulphate, filtrated and concentrated. The crude material was purified on silica (heptane/ethyl acetate), to give 2.7 g (77%) the subtitle compound as a colourless oil.

Workup

  1. customto reach room temperature
  2. stirringstirred over night
  3. customThe reaction was quenched with ammonium chloride (aq, sat)
  4. custompartitioned between water and ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltrated
  8. concentrationconcentrated
  9. customThe crude material was purified on silica (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-8c18a58d889846d2979008f65b8a549d
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07449475B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes